Category: Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

To a solution of (Z)-phenyl N’-cyano-N-(3,4-difluorophenyl)carbamimidate (286 mg, 1.05 mmol) and 2-(3-bromopropoxy)tetrahydro-2H-pyran (369 mg, 277 mu, 1.57 mmol) in DMF (10.5 mL) was added at room temperature under an athmosphere of nitrogen potassium carbonate (289 mg, 2.09 mmol). The suspension was heated to 85C over night. Additional 2-(3- bromopropoxy)tetrahydro-2H-pyran (140 mu, 0.8mmol) und potassium carbonate (145 mg, 1.05 mmol) was added and the reaction was heated for 5 hours to 85C. Water was added and the reaction was extracted twice with diethyl ether. The combined organic layers were washed with water and with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The title compound was obtained as a light yellow viscous oil (202 mg, 46%) after column chromatography on silica gel using a gradient of heptane/ethyl acetate 4: 1 to 1 : 1 (v/v) as eluent.MS ISP (m/e): 332.1 (100) [(M-THP+H)+], 416.3 (5) [(M+H)+].1H NMR (DMSO-D6, 300 MHz): delta (ppm) = 7.38 (t, 2H), 7.26 – 7.16 (m, 3H), 7.05 (m, 3H), 4.52 (t, 1H), 3.97 (t, 2H), 3.85 (m, 2H), 3.48 (m, 2H), 2.00 (pent, 2H), 1.79 (m, 1H), 1.68 (m, 1H), 1.55 (m, 4H)).

33821-94-2, 33821-94-2 2-(3-Bromopropoxy)tetrahydro-2H-pyran 2777988, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; BAUMANN, Karlheinz; GOETSCHI, Erwin; GREEN, Luke; JOLIDON, Synese; KNUST, Henner; LIMBERG, Anja; LUEBBERS, Thomas; THOMAS, Andrew; WO2011/92272; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

A mixture of methyl 6-(2,6-difluoro-4-hydroxyphenyl)-5-fluoropicolinate (1.0 equiv.), 4-(bromomethyl)tetrahydro-2H-pyran (2.0 equiv.) and K2CO3 (4.0 equiv.) in DMF (0.20 M) was heated at 100 C. for 20 min in microwave. The reaction mixture was cooled off to rt and partitioned between EtOAc and H2O. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give methyl 6-(2,6-difluoro-4-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)-5-fluoropicolinate in 100% yield. LC/MS=382.0 (MH+), Rt=0.97 min., 125552-89-8

The synthetic route of 125552-89-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Burger, Matthew; Ding, Yu; Han, Wooseok; Nishiguchi, Gisele; Rico, Alice; Simmons, Robert Lowell; Smith, Aaron R.; Tamez, JR., Victoriano; Tanner, Huw; Wan, Lifeng; US2012/225061; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

873397-34-3, Tetrahydro-2H-pyran-3-carboxylic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,873397-34-3

Treat a mixture of N-[1-(2,3-dihydro-1H-indol-5-yl)ethyl]-4-fluorobenzamide, Isomer 1 (Preparation 24A) (150 mg, 0.528 mmol), racemic tetrahydropyran-3-carboxylic acid (100 mg. 0.739 mmol) and N,N-diisopropylethylamine (0.277 mL, 1.58 mmol) in DCM (5.28 mL) with 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxid hexafluorophosphate (304 mg, 0.791 mmol). Stir at room temperature for 45 minutes. Dilute the reaction mixture with DCM. Add water and saturated aqueous sodium bicarbonate solution. Separate the layers and extract the aqueous layer twice with DCM. Pass the combined organic layer through a hydrophobic frit (ISOLUTE? phase separator cartridge) and concentrate the filtrate. Purify by silica gel column chromatography eluting with a gradient of 20-55percent acetone in hexanes to give the title compound (184 mg, 88percent) as a white solid. ES/MS (m/z): 397.2 (M+H).

As the paragraph descriping shows that 873397-34-3 is playing an increasingly important role.

Reference£º
Patent; Eli Lilly and Company; Bastian, Jolie Anne; Chen, Jiehao; Cohen, Jeffrey Daniel; Henry, James Robert; McMillen, William Thomas; Reaman, Bradley Earl; Rubio, Almudena; Sall, Daniel Jon; Zhao, Gaiying; (36 pag.)US2017/354641; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Production Example 1Dihydro-2H-pyran-3(4H)-one To a mixture of oxalyl chloride (2.28 mL, 26.6 mmol) and dichloromethane (40 mL) was added a mixture of DMSO (3.78 mL, 53.2 mmol) and dichloromethane (20 mL) while stirring at -78 C., and the mixture was stirred at -78 C. for 30 minutes. After then adding to this mixture a mixture of tetrahydropyran-3-ol (synthesized according to the method described in Tetrahedron, 60, 10411-10418, 2004) (136 g, 13.3 mmol) and dichloromethane (20 mL) at -78 C., the resulting mixture was stirred at -78 C. for 30 minutes, after which triethylamine (11.1 mL, 79.8 mmol) was added and stirring was continued for 2 hours while slowly raising the temperature to 0 C.Brine and diethyl ether were added to the mixture, and after sufficient shaking, the organic layer was separated and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was then filtered, and the solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (1.62 g, 162 mmol).1H-NMR (CDCl3) delta: 2.07-2.14 (m, 2H), 2.54 (t, J=6.8 Hz, 2H), 3.82-3.88 (m, 2H), 4.03 (s, 2H)., 19752-84-2

The synthetic route of 19752-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Eisai R&D Management Co., Ltd.; US2011/86882; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125552-89-8, 4-(Bromomethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Under argon atmosphere, a solution of the carbazole amide 67 (100mg, 0.36mmol), 1-bromo-3-methoxypropane (61muL, 0.54mmol), and Cs2CO3 (234mg, 0.72mmol) in DMF (10mL) was tightly capped in a 20mL microwave vessel. The mixture was subjected to microwave irradiation at 140C for 1h and then cooled to room temperature. The reaction mixture was diluted with EtOAc and filtered. The organic solvents were evaporated in vacuo. The residue was suspended in methyl tert-butyl ether (150mL), and the organic phase was washed with saturated aqueous sodium bicarbonate, brine, dried (MgSO4), filtered and evaporated in vacuo. The obtained residue was purified by column chromatography on silica gel eluting with EtOAc/heptanes in different proportions to give the title product (119mg, 95%) as a clear, colorless gum., 125552-89-8

125552-89-8 4-(Bromomethyl)tetrahydropyran 2773286, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Petrov, Ravil R.; Knight, Lindsay; Chen, Shao-Rui; Wager-Miller, Jim; McDaniel, Steven W.; Diaz, Fanny; Barth, Francis; Pan, Hui-Lin; Mackie, Ken; Cavasotto, Claudio N.; Diaz, Philippe; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 881 – 907;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

103260-44-2, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

c) To a solution of 425 mg (2.5 mmol) of ethyl 2-(tetrahydro-2H-pyran-4- yl)acetate in 10 mL of dry THF cooled at 05C under argon, a 2.71 mL of a solution of LiAII-U 1 M in THF was added. Bubbling was observed. It was stirred at room temperature for 30 min. Then it was quenched with wet EtAcO, dried with MgS04 and filtered through celite, washing with abundant EtAcO. After removing the solvent the desired compound, 2-(tetrahydro-2H-pyran-4-yl)ethanol, was obtained (300 mg, 93%).

103260-44-2, 103260-44-2 Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate 2773412, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; DRACONIS PHARMA, S.L.; ALMIRALL, S.A.; TORRENS JOVER, Andoni; MERCE VIDAL, Ramon; CALDENTEY FRONTERA, Francesc Xavier; RODRIGUEZ GARRIDO, Antonio, David; CARCELLER GONZALEZ, Elena; SALAS SOLANA, Jordi; WO2013/37960; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

101691-65-0, (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To tert-butyl 3-(5-chloro-2-fluoropyridin-4-yl)phenylcarbamate (270 mg, 0.837 mmol) in DMF (3 mL) was added slowly sodium hydride (60 wt.% in mineral oil, 40.1 mg) at 0 C. The ice bath was removed and the crude mixture was stirred for 20 min at room temperature. To the crude mixture was added (tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate (271 mg, 1.004 mmol) and stirring was continued at 40 C for 40 hrs. The reaction mixture was cooled to room temperature and diluted with EtOAc (150 mL). The mixture was washed saturated aqueous sodium bicarbonate solution (2x), water (2x) and brine (lx), dried with sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [silica gel, 24 g, EtO Ac/heptane = 0/100 to 30/70] providing [3-(5-chloro-2-fluoro-pyridin-4-yl)-phenyl]- (tetrahydro-pyran-4-ylmethyl)-carbamic acid tert-butyl ester (205 mg). LCMS (m/z): 421.2 [M+H]+; Rt = 1.19 min.

101691-65-0, As the paragraph descriping shows that 101691-65-0 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; PFISTER, Keith B; SENDZIK, Martin; WO2011/26917; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

720706-20-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.720706-20-7,(4-Amino-4-tetrahydropyranyl)methanol,as a common compound, the synthetic route is as follows.

Di-tert-butyl dicarbonate (6.39 g, 29.27 mmol) was added to triethylamine (3.70 g, 36.59mmol), (4-aminotetrahydro-2H-pyran-4-yl)methanol (3.2 g, 24.40 mmol) in THF (40 mL)under nitrogen. The resulting mixture was stirred at 70 C for 5 hours. The reactionmixture was quenched with water (50 mL), extracted with EtOAc (3 x 50 mL), the organic layer was then dried over Na2SO4, filtered and evaporated to afford yellow oil. The crude product was purified by flash silica chromatography, elution gradient 10 to 30% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford tert-butyl (4- (hydroxymethyl)tetrahydro-2H-pyran-4-yl)carbamate (4.20 g, 74%) as a white solid. ?HNMR (300 MHz, DMSO, 30C) 1.45 (9H, s), 1.50-1.84 (2H, m), 3.31-3.61 (6H ,m), 4.61- 4.66 (1H, m), 6.36 (1H, s). mlz (ES+), [M+H]+ = 232.

720706-20-7 (4-Amino-4-tetrahydropyranyl)methanol 18316484, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

To a stirred suspension of 3-bromo-N-(4-ethyl-phenyl)-4-hydroxy-N-isobutyl-benzenesulfonamide (11, 2.20 g, 5.34 mmol)and Cs2CO3 (3.48 g, 10.7 mmol) in DMF (44 mL), was added 4-(bromomethyl)tetrahydropyran (1.15 g, 6.40 mmol). The reactionmixture was stirred at 80 C for 16 h, cooled to r.t. and quenchedwith water (5.0 mL). The reaction mixture was extracted withEtOAc (2 50 mL) and the organic phases were combined, washedwith a saturated solution of sodium carbonate, brine, dried overMgSO4 and concentrated to dryness. The residue was trituratedwith heptane and the solid obtained was collected by filtration anddried to a constant weight in a vacuum oven at 40 C to afford thetitle compound (2.36 g, 87%) as a white solid: UPLC-MS(tR 1.52 min, purity 100%), ESI m/z 510.11/512.11 (MH); 1HNMR (400 MHz, CDCl3) d 7.77 (d, J 2.3 Hz, 1H), 7.46 (dd, J 8.6,2.3 Hz, 1H), 7.21e7.09 (m, 2H), 7.04e6.93 (m, 2H), 6.87 (d, J 8.6 Hz,1H), 4.07 (ddd, J 11.6, 5.0, 1.8 Hz, 2H), 3.94 (d, J 6.4 Hz, 2H), 3.50(td, J 11.6, 2.1 Hz, 2H), 3.29 (d, J 7.3 Hz, 2H), 2.67 (q, J 7.6 Hz,2H), 2.19 (m, 1H), 1.83 (m, 2H), 1.67e1.49 (m, 2H), 1.26 (t, J 7.6 Hz,3H), 0.93 (d, J 6.6 Hz, 6H)., 125552-89-8

The synthetic route of 125552-89-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Lafitte, Guillaume; Parnet, Veronique; Pierre, Romain; Raffin, Catherine; Vatinel, Rodolphe; Musicki, Branislav; Tomas, Loic; Bouix-Peter, Claire; Ouvry, Gilles; Daver, Sebastien; Arlabosse, Jean-Marie; Boiteau, Jean-Guy; Gerfaud, Thibaud; Harris, Craig S.; Tetrahedron; vol. 74; 40; (2018); p. 5974 – 5986;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

103260-44-2, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of lithium diisopropylamide (1.8 M in THF/heptane/ethylbenzne, 3.6 mL, 6.4 mmol) in 10 mL of THF at -78 0C was added trimethylsilyl chloride (1.4 mL, 11 mmol) dropwise via syringe pump. The product of Example 143B (1.0 g, 5.8 mmol) in 5 mL of THF was then added to the mixture dropwise via syringe pump. The mixture was stirred at -78 0C for 2 hours then N-bromosuccinimide (NuBS, 1.1 g, 6.0 mmol) in 10 mL of THF was added dropwise via syringe pump. The reaction mixture was allowed to warm slowly to ambient temperature and was stirred for 16 h. The mixture was then concentrated under reduced pressure and the residue was dissolved in 20 mL of EtOAc, washed 1 X 5 mL of H2O. The aqueous layer was extracted 3 X 5 mL of EtOAc and the combined organic extracts were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via column chromatography (SiO2, 70% hexanes in EtOAc) to provide the title compound (0.70 g, 2.8 mmol, 48% yield). MS (DCIZNH3) m/z 268 (M+NH4)+., 103260-44-2

As the paragraph descriping shows that 103260-44-2 is playing an increasingly important role.

Reference£º
Patent; ABBOTT LABORATORIES; WO2006/69196; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics